CA2676710A1 - Hydroxy polyesters and uses as demulsifiers - Google Patents
Hydroxy polyesters and uses as demulsifiers Download PDFInfo
- Publication number
- CA2676710A1 CA2676710A1 CA002676710A CA2676710A CA2676710A1 CA 2676710 A1 CA2676710 A1 CA 2676710A1 CA 002676710 A CA002676710 A CA 002676710A CA 2676710 A CA2676710 A CA 2676710A CA 2676710 A1 CA2676710 A1 CA 2676710A1
- Authority
- CA
- Canada
- Prior art keywords
- compositions
- group
- epoxide
- carboxylic
- hydroxyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 125000002887 hydroxy group Chemical group [H]O* 0.000 title claims abstract 10
- 229920000728 polyester Polymers 0.000 title claims abstract 10
- 239000000203 mixture Substances 0.000 claims abstract 14
- -1 epoxide compounds Chemical class 0.000 claims abstract 6
- 150000001875 compounds Chemical class 0.000 claims abstract 5
- 238000000034 method Methods 0.000 claims 9
- 238000006243 chemical reaction Methods 0.000 claims 3
- 125000003700 epoxy group Chemical group 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- 239000000839 emulsion Substances 0.000 claims 2
- 238000005886 esterification reaction Methods 0.000 claims 2
- 239000007787 solid Substances 0.000 claims 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 238000005119 centrifugation Methods 0.000 claims 1
- 239000010779 crude oil Substances 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 239000012535 impurity Substances 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 239000003921 oil Substances 0.000 claims 1
- 125000000962 organic group Chemical group 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
- 230000001988 toxicity Effects 0.000 claims 1
- 231100000419 toxicity Toxicity 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/11—Esters; Ether-esters of acyclic polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/40—Polyesters derived from ester-forming derivatives of polycarboxylic acids or of polyhydroxy compounds, other than from esters thereof
- C08G63/42—Cyclic ethers; Cyclic carbonates; Cyclic sulfites; Cyclic orthoesters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/88—Post-polymerisation treatment
- C08G63/90—Purification; Drying
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/52—Compositions for preventing, limiting or eliminating depositions, e.g. for cleaning
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/60—Compositions for stimulating production by acting on the underground formation
- C09K8/602—Compositions for stimulating production by acting on the underground formation containing surfactants
- C09K8/604—Polymeric surfactants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polyesters Or Polycarbonates (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Biological Depolymerization Polymers (AREA)
Abstract
Hydroxyl polyester compounds or compositions which arc useful as oilfield deinulsifiers are prepared through eslerifying carboxylic compounds and epoxide compounds under controlled molar ratios. The hydroxyl polyesters are useful as biodegradable demulsifiers on oil productions.
Claims (16)
1. A block type amphiphilic hydroxyl polyester composition is useful as demulsifiers, particularly as biodegradable demulsifies.
2. A star or branched type amphiphilic hydroxyl polyester composition is useful as demulsifiers, particularly as biodegradable demulsifies.
3. A process to prepare the hydroxyl polyester compositions claimed in claims 1 or 2, wherein the hydroxyl ester bond is formed by the reaction of one carboxylic compound with at least two carboxylic groups on molecule with at least one epoxide compound with monoepoxide group.
4. A process to prepare the hydroxyl polyester compositions claimed in claims 1 or 2, wherein the hydroxyl ester bond is formed by the reaction of one epoxide compound with -multi-epoxide groups on molecule with at least one carboxylic compound with at least one carboxylic group.
5. A process to prepare the hydroxyl polyester compositions claimed in claims 1 or 2, wherein the esterification reactions between epoxide compounds and carboxylic acid compounds are carried out in melt, solution or solution mixtures.
6. A process in claims 3 or 4, wherein the carboxylic acid group is a molar excess to another reactive organic group, i.e. epoxide group.
7. A process in claims 3 or 4, wherein the molar ratio of carboxylic group to epoxide group is from 1.90:1 to 1.01:1.
8. A process to prepare the hydroxyl polyester compositions in claims 3 or 4 is carried out at a temperature from room temperature to 200°C at ambient pressure with or without addition of catalyst.
9. A process in claims 3 or 4, wherein the esterification reaction temperature is between 60 and 150°C without addition of catalyst.
10. A process in claims 3 or 4, wherein one filtration or centrifugation step is applied to remove unreacted compounds or impurities.
11. A process in claims 3 or 4, wherein extra amount of small molecular carboxylic acid, such as propionic acid, is used to increase the conversion of epoxide group in order to improve the toxicity of the products.
12. The compositions as claimed in claims 1 or 2 are viscous liquid, soft solid, solution in organic solvents or solid powder.
13. The compositions as claimed in claims 1 or 2 have a molecular weight greater than from about 500 kg/mole.
14. The compositions as claimed in claims 1 or 2 wherein said compositions are useful as demulsifiers effective in demulsifying water-in-oil emulsions, particularly crude oil emulsions.
15. The compositions as claimed in claims 1 or 2, wherein said compositions are biodegradable demulsifiers.
16. A biodegradable demulsifier comprising the hydroxyl polyesters claimed in claims 1 or 2.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US89105407P | 2007-02-22 | 2007-02-22 | |
| US60/891,054 | 2007-02-22 | ||
| PCT/US2008/053379 WO2008103564A1 (en) | 2007-02-22 | 2008-02-08 | Hydroxy polyesters and uses as demulsifiers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2676710A1 true CA2676710A1 (en) | 2008-08-28 |
| CA2676710C CA2676710C (en) | 2012-04-17 |
Family
ID=39710435
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2676710A Expired - Fee Related CA2676710C (en) | 2007-02-22 | 2008-02-08 | Hydroxy polyesters and uses as demulsifiers |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7884137B2 (en) |
| EP (1) | EP2113010A4 (en) |
| AR (1) | AR065448A1 (en) |
| BR (1) | BRPI0807561A2 (en) |
| CA (1) | CA2676710C (en) |
| EA (1) | EA019758B1 (en) |
| MX (1) | MX2009009018A (en) |
| WO (1) | WO2008103564A1 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX340805B (en) | 2011-04-18 | 2016-06-24 | Inst Mexicano Del Petróleo | Synergistic formulations of functionalized copolymers and ionic liquids for dehydrated and desalted of median, heavy and extra heavy crude oils. |
| CN108517204A (en) * | 2018-04-11 | 2018-09-11 | 扬州润达油田化学剂有限公司 | A kind of three-in-one acidification blocking remover and its application process for de-plugging of well |
| US20220041803A1 (en) * | 2018-12-11 | 2022-02-10 | Nouryon Chemicals International B.V. | Polyester demulsifier |
| CN109851795A (en) * | 2018-12-24 | 2019-06-07 | 陕西科技大学 | A kind of branched polysiloxane thick oil demulsifier and preparation method thereof |
| CN113121351B (en) * | 2019-12-30 | 2022-07-12 | 江苏苏博特新材料股份有限公司 | Efficient concrete foam stabilizer and preparation method thereof |
| CN113667023B (en) * | 2021-08-24 | 2023-01-17 | 长江大学 | Amino-functionalized paper, demulsifier, and preparation method and application thereof |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1570825B2 (en) * | 1965-11-16 | 1973-10-04 | Ernst Jaeger Fabrik Chem. Rohstoffe Gmbh, 4000 Duesseldorf-Reisholz | Process for the production of fatty acid-modified polymers |
| NL127440C (en) * | 1966-02-22 | |||
| GB1277204A (en) * | 1968-08-15 | 1972-06-07 | Secr Defence | Improvements in epoxide reactions |
| US3859318A (en) * | 1969-05-19 | 1975-01-07 | Lubrizol Corp | Products produced by post-treating oil-soluble esters of mono- or polycarboxylic acids and polyhydric alcohols with epoxides |
| US4032514A (en) * | 1971-08-18 | 1977-06-28 | Petrolite Corporation | Oxyalkylated cyclic phenol-aldehyde resins and uses therefor |
| US3813339A (en) * | 1972-08-02 | 1974-05-28 | Emery Industries Inc | Acid-terminated hydroxy ester compounds as lubricating oil additives |
| US5057617A (en) * | 1988-11-07 | 1991-10-15 | Exxon Chemical Patents Inc. | Dispersant additives prepared from monoepoxy thiols |
| DE3927638A1 (en) * | 1989-08-22 | 1991-02-28 | Hoechst Ag | AMINE-FREE ESTERIFIED GLYCIDYL ETHER ADDITION PRODUCTS AND THEIR USE |
| NL9200416A (en) * | 1992-03-06 | 1993-10-01 | Dsm Nv | HYPER BRANCHED POLYMERS AND A PROCESS FOR THE PREPARATION OF HYPER BRANCHED POLYMERS. |
| DE4326772A1 (en) * | 1993-08-10 | 1995-02-16 | Basf Ag | Reaction products from olefinically unsaturated carboxylic acids and polyetherols and their use as demulsifiers for crude oil emulsions |
| US5609794A (en) * | 1994-08-05 | 1997-03-11 | Exxon Chemical Patents, Inc. | Demulsifier for water-in-oil emulsions, and method of use |
| SE503342C2 (en) * | 1994-10-24 | 1996-05-28 | Perstorp Ab | Polyester-type hyperbranched macromolecule and process for its preparation |
| DE4441363A1 (en) * | 1994-11-21 | 1996-05-23 | Huels Chemische Werke Ag | Amphiphilic compounds with at least two hydrophilic and at least two hydrophobic groups based on di, oligo or polyol ethers |
| US5540743A (en) * | 1994-12-30 | 1996-07-30 | Chevron Chemical Company | Polyalky and poly(oxyalkylene) benzyl amine esters and fuel compositions containing the same |
| US6689724B2 (en) * | 1996-09-13 | 2004-02-10 | Exxonmobil Research And Engineering Company | Antioxidants and antioxidant boosters capable of producing hydroperoxyl radicals |
| DE19717264A1 (en) * | 1997-04-24 | 1998-10-29 | Huels Chemische Werke Ag | Amphipolar compounds with at least two hydrophilic and at least two hydrophobic groups based on di, oligo- or polyenes |
| WO1999010309A1 (en) * | 1997-08-25 | 1999-03-04 | Cognis Deutschland Gmbh | Method for producing alkylene glycol esters with limited homologue distribution |
| DE19834360A1 (en) * | 1998-07-30 | 2000-02-03 | Bayer Ag | Process for the preparation of esters of (meth) acrylic acid |
| US7018957B2 (en) * | 2003-02-21 | 2006-03-28 | Bj Services Company | Method of using high molecular weight demulsifiers |
| US7217779B2 (en) * | 2003-03-14 | 2007-05-15 | Nalco Company | Phosphoric ester demulsifier composition |
| DE10329723B3 (en) * | 2003-07-02 | 2004-12-02 | Clariant Gmbh | Using alkoxylated dendritic polyesters as emulsion breakers, especially in crude oil recovery, are required in only small amounts and are biodegradable |
| US7470744B2 (en) * | 2006-04-12 | 2008-12-30 | Baker Hughes Incorporated | Copolymers useful as demulsifiers and clarifiers |
-
2008
- 2008-02-08 BR BRPI0807561-1A patent/BRPI0807561A2/en not_active IP Right Cessation
- 2008-02-08 MX MX2009009018A patent/MX2009009018A/en active IP Right Grant
- 2008-02-08 EA EA200970785A patent/EA019758B1/en not_active IP Right Cessation
- 2008-02-08 CA CA2676710A patent/CA2676710C/en not_active Expired - Fee Related
- 2008-02-08 EP EP08729351A patent/EP2113010A4/en not_active Withdrawn
- 2008-02-08 WO PCT/US2008/053379 patent/WO2008103564A1/en active Application Filing
- 2008-02-22 US US12/035,745 patent/US7884137B2/en not_active Expired - Fee Related
- 2008-02-22 AR ARP080100750A patent/AR065448A1/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| US20080207780A1 (en) | 2008-08-28 |
| EP2113010A4 (en) | 2012-05-23 |
| WO2008103564A1 (en) | 2008-08-28 |
| BRPI0807561A2 (en) | 2014-07-01 |
| EA019758B1 (en) | 2014-06-30 |
| MX2009009018A (en) | 2009-09-03 |
| EP2113010A1 (en) | 2009-11-04 |
| US7884137B2 (en) | 2011-02-08 |
| AR065448A1 (en) | 2009-06-10 |
| EA200970785A1 (en) | 2010-02-26 |
| CA2676710C (en) | 2012-04-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20180208 |